- Anachronisms: At the end of the movie, a radio announcer refers to a pass as a 'Hail Mary.' The term was coined by Roger Staubach in 1975, referring to his pass at the end of a Dallas Cowboys game on December 28, 1975.
- Anachronisms: When we first meet Lexie Littleton, she lights up a filtered cigarette in her boss's office. Filtered cigarettes were not widely available until the mid 1950s.
- Anachronisms: On the train, one of the Leatherheads leaves the restroom while zipping up his fly. The movie takes place in 1925; zippers were not used as closures on men's trousers until the 1930s.
- Revealing mistakes: At the end of the movie, the series of newspaper headlines state some related information, but all of the articles contain generic paragraphs, none of which have anything to do with the headline or the plot. Other headlines on the pages appear multiple times, such as "KING IN NEST OF SHRINES", taken from the New York Times' 1923 article on the opening of Tutankhamen's tomb.
- Factual errors: There are several key historical errors. The NFL already had a league president in 1925 (Joe Carr), and he was not appointed by Congress. Moreover, he would not have had the power to deal with the media as he does in the film.
- Anachronisms: In the scene where they are being chased through the building after leaving the speakeasy, a glass and blue lit modern "exit" sign was clearly visible above the doorway. Also, modern fire sprinklers where seen in the ceiling of the same shot.
- Anachronisms: In the scene where they are leaving the commissioner's office, they get in an elevator and push a button to go to the ground floor. All elevators at that time had operators who controlled elevator movement. Push buttons did not come in to use until the 1950's.
- Revealing mistakes: After Carter and Dodge have repeatedly and for an extended period of time punched each other in the face, neither has any marks whatsoever at the end of the fight.
- Continuity: Just before the police raid the speak easy. Lexie and Dodge are having a drink and Lexie's hand changes position between camera angles. Her hand is up then down and back and forth between camera shots.
- Anachronisms: In a wide shot over the stadium during the final game, modern freight cars are seen in the distance.
- Anachronisms: In his radio interview, Carter supposes his running skills were learned "from dodging those Jerries" in the war. The term 'Jerry' was not in popular usage until WWII.
- Factual errors: This movie takes place in 1925. The idea of an annual college draft in the NFL was not proposed until 1935 and wasn't put in effect until 1936.
- Anachronisms: The film is set in 1925 but the singer in the speakeasy croons the Gershwin standard, "The Man I Love," which debuted in the 1927 musical "Strike Up the Band."
- Anachronisms: Early in the film as the actors are walking across a street, a 1928-29 Ford Model A drives by. The film takes place in 1925, therefore it should have been a Model T like the rest of the cars used.
- Errors made by characters (possibly deliberate errors by the filmmakers): When Dodge and Lexie dance in the speakeasy, he leads with his right hand. Men always lead with their left hand.
- Continuity: In the opening scene when Carter Rutherford scores a touchdown for Princeton he runs before a packed house. Yet, when he's mobbed after scoring, empty terraces can be seen behind the first few rows of fans.
- Incorrectly regarded as goofs: Lexie reports that Duluth has beaten a woeful Pottsville team. However, the 1925 Pottsville Maroons only lost two games that season, to Frankford and Providence, on their way to beating Chicago in the League Championship. Nonetheless, the movie is a fictional story, as this movie is a fiction and need not adhere to historical match records.
- Continuity: The right horn of the cow on the field is first against his ear, then, the next time we see him, it's behind his ear.
- Errors made by characters (possibly deliberate errors by the filmmakers): The job placement worker asks Dodge if he learned a trade while he served in the war, then rhetorically asks how has he earned a living in the last 20 years without a marketable skill. The war ended 7 years before the story takes place.
- Revealing mistakes: In the movie's final scene, no motorcycle engine noise can be heard. An electric replica motorcycle was used for filming, so all engine sounds had to be dubbed.
- Anachronisms: When Dodge and Lexie are fleeing the police after leaving the speakeasy, they go under a doorway with an electrically lit exit sign glowing bright red.
- Factual errors: At beginning of film in newspaper editors office, Lexie Littleton (Renée Zellweger) is smoking a 'filtered' cigarette. Only non-filtered smokes were available in 1925.
- Errors made by characters (possibly deliberate errors by the filmmakers): Early in the movie, on the bus, Carter tells Lexie he is 24. The movie takes place in 1925. If Carter was in the war in 1917-1918, he would have been 16 or 17, and most likely still in high school.
- Factual errors: At one point in the movie someone says that Duluth has beaten Pottsville. However, the 1925 Pottsville Maroons only lost two games that season, to Frankford and Providence, on their way to beating Chicago in the League Championship. The League stripped the Maroons of their title after Pottsville defeated a Notre Dame team that included the Four Horsemen. At the time, it was widely recognized that Pottsville helped legitimize the fledgling league by not only beating the best team ever fielded up to that point, but through their use of a professional, team-oriented approach to their play, instead of the barnstorming methods employed up to that point.
- Continuity: During the bar fight between the football players and the Army men, the piano player is first shown playing while the fight is going on, a few shots later the piano player is shown and has a bottle now sitting on the keyboard (which he smashes over someone next to him).
>>> WARNING: Here Be Spoilers <<<
Goofs below here contain information that may give away important plot points. You may not want to read any further if you've not already seen this title.
- Continuity: SPOILER: After the 'Sgt. York' play, Jimmy (George Clooney) is doused with water, revealing his Duluth uniform. When he walks away from the mob, the front of his jersey is still covered with mud. In his ensuing conversation with Carter (John Krasinski), the partially-shown jersey is again rinsed off enough to reveal its color.
- Plot holes: SPOILERS: The story takes place in 1925. America entered World War I in April 1917 when Congress, at the request of Woodrow Wilson, declared war against Germany. The war ended with the Armistice in November 1918. Even if Carter had been a freshman when he joined the Army, he would have finished his studies by 1921 or 1922. In short, he still wouldn't be at Princeton in 1925.
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